6533b7d8fe1ef96bd126a3ac

RESEARCH PRODUCT

Synthesis of nucleoside and nucleotide conjugates of bile acids, and polymerase construction of bile acid-functionalized DNA.

Miloslav SandaHana Macíčková-cahováMichal HocekSatu IkonenSatu IkonenRadek Pohl

subject

medicine.drug_classDNA-Directed DNA PolymeraseThermococcaceaeNucleic Acid DenaturationBiochemistryPrimer extensionBile Acids and Saltschemistry.chemical_compoundmedicineNucleotidePhysical and Theoretical ChemistryPolymerasechemistry.chemical_classificationbiologyBile acidNucleotidesOrganic ChemistryCholic acidNucleosidesDNAEnzymechemistryBiochemistrybiology.proteinNucleosideDNA

description

Aqueous Sonogashira cross-coupling reactions of 5-iodopyrimidine or 7-iodo-7-deazaadenine nucleosides with bile acid-derived terminal acetylenes linked via an ester or amide tether gave the corresponding bile acid–nucleoside conjugates. Analogous reactions of halogenated nucleoside triphosphates gave directly bile acid-modified dNTPs. Enzymatic incorporation of these modified nucleotides to DNA was successfully performed using Phusion polymerase for primer extension. One of the dNTPs (dCTP bearing cholic acid) was also efficient for PCR amplification.

10.1039/b924072ahttps://pubmed.ncbi.nlm.nih.gov/20165813